In 2003, Bob appeared on the first season of The Bachelorette with Trista Sutter, but there was no romance between them.

Trista was in a relationship with Ryan Sutter. The couple has been married for over 14 years and shares two kids together.

Meanwhile, Bob the Bachelor in the following year. At the time, he was linked with Estella Gardinier. Instead of an engagement ring, Bob gave her a promise ring. Unfortunately, they called it quits after the show aired.

Bob was previously married to All My Children actress Rebecca Budig. They got married in July 2004 at his family's home in Long Lake, Michigan. However, after six years of marital relationship, they finalized their divorce on 23 July 2010.

In 2016, Bob announced that he was set to marry Jessica Canyon. The couple's wedding ceremony took place on 11 November 2016 in Punta Mita, Mexico on his father's birthday.